


(My) Pretty Boy

by blurrycopaface



Category: Twenty One Pilots
Genre: Comfort, Crossdressing, Femininity, Gender Roles, Jenshler, Multi, Polyamory, Pregnant Jenna
Language: English
Status: Completed
Published: 2020-07-19
Updated: 2020-07-19
Packaged: 2021-03-05 06:20:14
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,801
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25159873
Author URL: https://archiveofourown.org/users/blurrycopaface/pseuds/blurrycopaface
Summary: Remember when Jenna called Tyler her pretty boy, cause I sure do.
Relationships: Jenna Black/Josh Dun/Tyler Joseph, Jenna Black/Tyler Joseph, Josh Dun/Debby Ryan, Josh Dun/Tyler Joseph
Comments: 4
Kudos: 20





	(My) Pretty Boy

It had started out as a joke, mostly.

Jenna had been the one to suggest it. “It would be so perfect, Tyler. I even have the right shade of hair for her!”

They sat watching the Grinch and Jenna was pointing towards the screen as Cindy Lou Who sang, ‘Where Are You Christmas’. 

Tyler watches his wife twirl an inch of her own blonde hair that did, indeed undeniably match the character’s own.

It would be perfect, almost _too_ perfect. 

So Tyler shook his head, exclaiming, “Oh no, I _obviously_ have to be Cindy Lou, Jenna, c’mon.” 

Jenna laughs, “And would _I_ be the Grinch?” Her eyes sparkle with a tell tale mischief. 

He briefly gets an image of himself inserted into the movie, wearing the huge Mickey Mouse looking mittens and too large hair piece. Tyler grins and nods rather excitedly. 

He adjusts on the couch, swinging a leg over his knee and rubbing at it. “I would need to shave my legs again though, and find a wig...Do they even make wigs like that?” 

He’s sort of lost in trajectory of thought as he glances back towards Jenna. 

And she, being the beautiful and perfect wife she was, just beams at Tyler and replied, “We can do that.” 

It started as a joke, but jokes always have some basis in reality, right? 

—— 

The Halloween party was going to take place in downtown Los Angeles in an hour and thirty two minutes (Tyler was counting) and he was nervous they wouldn’t finish putting their costumes together in time. Jenna still had a lot of green to put all over her body. And Tyler had, well; Tyler hadn’t even _seen_ his costume yet. 

The dress, cape and mitts were easy for Jenna to find; the wig, a little harder. 

“Where did you even get everything?” 

Tyler had asked after she declared she had purchased everything for the whole ensemble. 

“Amazon.” She says plainly. 

Tyler rolls his eyes. “Oh, of course.” 

She wouldn’t let him see it when it arrived, insisting that it should be a surprise. 

And so he sifts through the bag of items immediately once Jenna does grant him access to them Halloween night, pulling out the dress first, which piqued Tyler’s interest more than anything else. 

It was soft with checkered black, grey and white pattern, cut low at the chest with thin straps on the shoulders and a gauzy white underside that fanned out from the bottom. 

Tyler rubs his hands across it, mesmerized. He had never thought too much about women’s clothing, besides what looked attractive on his wife, but there was something illicitly exciting about wearing something normally deemed just for the opposite sex. He always enjoyed wearing the kimono, leggings and other ‘female’ clothes onstage. 

It felt empowering to him, affirming even, he never questioned that very much. And this wouldn’t be so different. 

But this time he would be wearing _makeup and a dress._

He inhales in a decidedly calm fashion and continues.

Next he took out the wig, it was platinum blonde and done up ridiculously just like Cindy Lou Who. 

Tyler laughs softly, wondering how much effort it took to style fake hair into this shape. 

_This is going to be so hilarious._

Lastly he sees the high platform black shoes, which were glossy and looked dangerous to walk in. 

“Go ahead, go get changed.” Jenna had demanded more than suggested in the adjoining dress room of their bedroom. 

Tyler secludes himself to the privacy of the restroom in order to get dressed up. The dress was so soft but it was so tight on him. 

His shoulders were far too wide and hips too narrow to properly fill it’s shape out. He felt awkward and adjusted the waist in eneresty. 

Was this how it was supposed to fit? Man it showed _so_ much skin. 

Tyler breaths out awkwardly, feeling his face flush a little. 

Next he slips the white socks on and buckles the large shiny shoes, tottering to stand up in them without falling over. 

“Jenna?” He calls to the other room, a little shakily. She rounds the corner a moment later, a brilliant green color. 

Tyler is caught off guard and bursts into laughter. “Oh man you look...you look great.” She’s dressed in a full furry green suit, with green paint on her face and yet she still managed to somehow look lovely.

She eyes him up and down and responds with, “You don’t look half bad yourself.”

“Jenna, these are really hard to walk in. How do you do this?” 

He falls forward as he asks this, his wife darting out a hand to help hold him. She grins, teeth bright white against her green makeup.

“You’ll be fine, it just takes a moment to get used to. Go slowly.” Tyler squeezes her hand in appreciation, inching out of the doorway into the main part of the bathroom. 

Here is where all the mirrors were, so Tyler self appreciatively could get a good 360 of himself. He couldn’t stop staring at the person he saw, or rather he was transfixed by his own image looking so contrary to his normally more masculine presentation. 

He sways his hips, seeing how the dress flowed around his ankles like a rush of ocean water, flattening his hands down the soft fabric.

Once distracted from the mirror and with help from Jenna, he situated himself into the chair in the middle. 

She brushes the makeup across his cheek, her perfume fills his nostrils. 

Tyler sucks in a breath and decides to speak his mind, something he finds rather terrifying at times. 

“Jenna.” She hums an acknowledgment. 

“How...would you describe when you feel pretty?” 

She takes a moment to consider this question, pausing to purse her green colored lips and then returning to delicately placing the lashes on his upper eyelids. “Well, it depends on the person. For someone it might feel like a softness or vulnerability in demeanor, a collected and refined attitude. For others it’s fire and power, sensuality, uncouthness.” 

Tyler jerks as he is startled by Jenna’s finger suddenly against his eye again. 

“Be still!” She scolds and he straightens up. 

There was a moment of silence as he ruminates on his wife’s words. He isn’t sure what she would say next, but he speaks his mind again anyway. 

“I think...that’s how I feel right now.” 

Even with eyes closed, Tyler can hear the smile in her voice as she says, “Well I think that’s lovely, Tyler.” 

They are posing in the corner, taking pictures for Instagram, and Tyler’s heart flutters because he actually feels very cute. 

The blush on his cheeks and long eyelashes Jenna had glued to his eyelids made his entire face look incredibly soft and feminine. Tyler blinks a few times in the mirrors and runs a hand across his cheek, fingers left with a small coating of glittery pink. 

“Don’t touch!” Jenna pokes at his arm and he grins sheepishly. She then slips the gloves onto his hands, which were the final touches to his outfit and they exit out of the door, Tyler rather unsurely in his heels. 

—- 

Josh looks pretty funny: white starchy wig over his naturally brown and curly head, hawaiin print shirt and baggy metallic pants.

Tyler wants to laugh, Josh stares at him from afar for a heatedly long moment, then smiles and waves, approaching them. 

“Wow - Tyler you look - I mean - you look _amazing_.” And Tyler knew he must be blushing now. 

Debby and Jenna were talking, he watches his wife sip sparkling water, Debby laughing and bouncing her perfectly wavy hair. They were both elegant and beautiful and Tyler felt a strange desire to go and be with them, to feel included in the prescience of women.

He turns his attention instead to Josh who is next to him, leaning on the wall and looking his way with smoldering eyes. 

“I meant it.” 

Tyler drinks his martini. “Meant what?” 

Josh grins, “When I said you looked amazing.” 

Tyler feels himself flush again and smiles, turning away from Josh to bite at his own lip and laugh through it. “You really do.” Josh continues. 

“Thank you.” His voice feels uncharacteristically wavering and delicate.

He clears his throat to attempt some of his usual composure. “The mittens really bring it together, huh?” Josh laughs, sounding so familiar and calming. 

Tyler laughs with him, then softening to gaze at his best friend again. 

Josh had really become muscular over the years, he had always been the more broad shouldered active one, but this was apparent much more to Tyler right now. Josh’s beard was growing out too and Tyler feels rather small and effeminate next to him, smooth hairless legs and face, rather thin arms and torso, dolled up in heels and a dress. 

He notices Josh staring at him still, in a way he had never really seen Josh stare af him, he bit his lip in a way too that made Tyler’s already buzzing head spin. 

Moments later Josh kisses him right on the mouth, grips slightly at his hips, pulls him against him. Tyler wasn’t used to being with him like this, normally he felt more in control, but the mixture of the booze and his lessened sense of masculinity, Tyler utterly succumbed to Josh’s guiding dominance.

It felt so strange. Not bad. Just strange.

He feels Josh pressing against the front of his dress and everything was so much, almost too much. He breaks away from him for a gasp of oxygen, looking around the party startedly, hoping no one they knew had seen them. Tyler can’t really take Josh seriously in his costume and laughs breathily while shifting weight back and forth on his heels, feeling more flustered than he had the beginning of the party. 

“I’m a lil tipsy.” He mumbles to Jenna as he stumbles to her rather awkwardly. 

She flashes a dazzling white smile and pulls out her phone. Tyler grips at his martini glass through his mitts, lifting it up to his face to sip as he looks into the camera for a cute pose.

Jenna giggles and taps at her phone, she turns the screen towards him to show that she was posting the picture to her Instagram story. 

Tyler wonders if he will regret that later. He doesn’t care. 

\---- 

“Did you have a good time at the party?” Jenna asks him. 

Tyler is removing the wig which was feeling really heavy and nods his head. 

“Yeah.” He strips the dress and folds it half heartedly into a basket. 

“Josh seemed to really enjoy it too.” 

Tyler blinks, looking at her with big eyes. “What is that supposed to mean?” His head throbbed, due to his lightweight strength towards spirits.

Jenna smirks, wiping green off her face so Tyler could see her pink plump lips purse when she says, “Oh, you know. He _really_ liked your costume.” 

Tyler flushes a hot red and struggles to get the damn shoes unbuckled. 

“I’m just glad to be home, the crowd started to get to me.” 

Jenna removes the green makeup and fur costume pieces from her person and Tyler appreciatively rubs at her exposed swollen stomach. 

“How is she?” He asks. “I missed her. Do you think she could breath under all that fur?” 

Jenna runs fingers through his hair and tugs at it. 

Tyler feels his eyes slip closed, next to Jenna on their bed, he feels the creeping edges of tiredness on his brain.

“Tyler?” 

“Mm?” Another small tug.

“You should take that makeup off.” 

He groans. Girls have it hard.

—— 

It was Christmas Eve and Tyler still thinks about the dress. The heels. The way his shoulders and hips looked and felt in the wrapping of the soft fabric.

“Jenna c-can I _uh-_ “ he swallows, it wasn’t like him to stutter. 

He fidgets with a pencil between his fingers and presses the end to his mouth nervously.

“Would you put makeup on me again? Like on Halloween?” 

And being the beautiful and perfect wife she was, just smiles and nods. “Of course.” 

Debby hadn’t been able to come because of something pertaining to a show she was a part of and an obligatory appearance at some event. 

It was fine with Tyler, he preferred it be just the three of them anyway. 

Josh wore a comfortable outfit of baggy soft sweatpants and Jenna wore a skirt that was tight and brown. 

Tyler felt almost out of place with the two of them dressed so casually, when he came rounding the corner, demanding the room’s attention in the flowing checkered fabric. Josh’s head shot up to meet his entrance.

He sees him flush slightly and Tyler grins, feeling powerful.

“Hey.” His voice was more sure this time.

“Hey.” Josh returns.

They ate a meal, Jenna’s home cooking was always incredibly satisfying, unless she tried to sneak something healthy in then Tyler would analyze the meal to pick out anything like a tomato or dried piece of fruit. 

Tyler crosses his legs, running his hand across them which felt satisfyingly soft after shaving them again earlier that day. 

“Ty, be careful not to get sauce on that dress.” Jenna warns him. 

Then Josh and him were giggling for whatever reason, all three squished together on the love seat, Tyler between the two of his favorite people in the whole entire world. 

A movie or show was playing, Josh had a can of something in his hand and was smiling and making Tyler laugh so hard his chest threatened to stretch the seams against the tight fitting dress.

Josh rubs Jenna’s stomach gently and Tyler places his hand atop his to trace the movements. “She kicked!” Josh proclaims and grins with a huge perfect smile, one that nearly matched Jenna’s own. 

Before he realized, Jenna was turning Tyler’s face to her with her hand and kissing him softly. Which led to him sinking into the state of an elevated high transcendent emotion, eager as ever to receive affection and soft touch, floating like a petal on the wind. 

“Do you feel pretty?” He hears the words and feels a jolt of almost fear; self doubt, hatred, critical judgement threatening to flood through Tyler’s brain. 

All the times he has felt so different from his family, different from the rest of the world, flashes through his cerebral cortex. He was not allowed to be weak, to be sensitive. And certainly not allowed to be _feminine._

But this was safe and he knew that.

So he nods, Jenna’s eyes as blue and expansive as the sky. 

“Yes.”

Jenna smiles at him and tugs his hair. 

“Well you are.” 

Tyler didn’t understand how liberating it truly was to let go until he wrote a song and sang it out loud in front of his family for the first time. He never thought he would ever feel more limitless, validated and free. Then he performed with Josh for the first few times and decided _that_ was the most important experience he had regarding freedom.

But something about what was happening in these small simple moments almost triumphed those times all together. He didn’t feel quiet himself: dressed up and adopting into a new way he never really had in his lifetime, but he simultaneously felt more authentic than he had in possible years. 

To feel so utterly freed from his normal day to day persona of strictly expected masculinization, something he often feels exhausted by wearing a mask of. It was like he was breathing an exhilarating air of liberated identity.

To be told he was _pretty;_ that was something his upbringing had never allowed him to conceive was even attainable, or applicable for him to be described as.

He wonders why more people don’t try to feel beautiful, or don’t make the effort to tell others the same.

And why, he wonders deeper still, why it had taken him so long to release the reins of what labels were okay to place on his body and identity and why he hadn’t done so sooner.

Hands were brushing against the smooth expanse of his legs, across the white ruffles peeking out from under the dress. 

_His_ dress, he corrects in his mind. 

Tyler’s eyes flutter closed, surrendering from pressure, from expectations, from control. 

He lets out a long breath through his nose as Jenna presses her soft silky lips to his neck, shudders as Josh’s contrasted stubble pricks across his collarbone. “Pretty boy.” 

Jenna’s voice is so soft and soothing to his left, warm against his ear. 

And on the other side of him, Josh’s low, husky tone responds to her with, “The prettiest boy in the world.” 

And Tyler believes it.

**Author's Note:**

> i mean, c’mon, we all know Tyler was _feeling_ himself


End file.
